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RU2015125076A - C6-C18-Acylated Hyaluronic Acid Derivative, METHOD FOR ITS PRODUCTION, NANOMICELLER COMPOSITION BASED ON IT, METHOD FOR ITS PRODUCTION AND METHOD FOR PRODUCING STABILIZED NANOMIZELIA - Google Patents

C6-C18-Acylated Hyaluronic Acid Derivative, METHOD FOR ITS PRODUCTION, NANOMICELLER COMPOSITION BASED ON IT, METHOD FOR ITS PRODUCTION AND METHOD FOR PRODUCING STABILIZED NANOMIZELIA Download PDF

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RU2015125076A
RU2015125076A RU2015125076A RU2015125076A RU2015125076A RU 2015125076 A RU2015125076 A RU 2015125076A RU 2015125076 A RU2015125076 A RU 2015125076A RU 2015125076 A RU2015125076 A RU 2015125076A RU 2015125076 A RU2015125076 A RU 2015125076A
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hyaluronic acid
production method
water
acylated
acid
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RU2015125076A
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RU2640287C2 (en
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Даниэла СМЕЖКАЛОВА
Глория ХУЭРТА-АНГЕЛЕС
Мартин БОБЕК
Мартина ХЕРМАННОВА
Люси ВИСТЕЖНОВА
Ярослав НОВОТНЫЙ
Ева ПРИКОПОВА
Кристина НЕСПОРОВА
Мирослава НЕМКОВА
Клара СЛЕЗИНГЕРОВА
Яромир КУЛХАНЕК
Дагмар КОЗИКОВА
Яна СОГОРКОВА
Ян КУЦЕРА
Павел КЛЕЙН
Владимир ВЕЛЕБНИЙ
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Контипро Биотек с.р.о.
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Claims (42)

1. С6-С18-ацилированное производное гиалуроновой кислоты общей формулы (I):1. C 6 -C 18 acylated derivative of hyaluronic acid of the general formula (I):
Figure 00000001
Figure 00000001
 где R представляет собой H+ или Na+ и R1 представляет собой H или -С(=O)CxHy или -C(=O)CH=CH-het, где x представляет собой целое число в диапазоне от 5 до 17, и y представляет собой целое число в диапазоне от 11 до 35, и CxHy представляет собой неразветвленную или разветвленную, насыщенную или ненасыщенную C5-C17 цепь, и het представляет собой гетероциклическую или гетероароматическую группу с произвольным содержанием атомов N, S или О, по меньшей мере с одной повторяющейся единицей, содержащей одну или несколько R1 -С(=O)CxHy или -C(=O)CH=CH-het групп, и где n находится в диапазоне от 12 до 4000.where R represents H + or Na + and R 1 represents H or -C (= O) C x H y or -C (= O) CH = CH-het, where x is an integer in the range from 5 to 17, and y is an integer ranging from 11 to 35, and C x H y is a straight or branched, saturated or unsaturated C 5 -C 17 chain, and het is a heterocyclic or heteroaromatic group with an arbitrary atomic content of N, S or O with at least one repeating unit containing one or more R 1 -C (= O) C x H y or -C (= O) CH = CH-het groups, and where n is in the dia range from 12 to 4000. 2. С6-С18-ацилированное производное гиалуроновой кислоты по п. 1, характеризующееся тем, что R представляет собой Н+ или Na+, и R1 представляет собой -С(=O)(СН2)7-СН=СН-(СН2)7-СН3.2. A C 6 -C 18 acylated derivative of hyaluronic acid according to claim 1, characterized in that R is H + or Na + , and R 1 is —C (= O) (CH 2 ) 7 —CH = CH - (CH 2 ) 7 -CH 3 . 3. Способ получения производного гиалуроновой кислоты общей формулы (I), отличающийся тем, что осуществляют взаимодействие гиалуроновой кислоты с С6-C18-карбоновой кислотой, активированной хлоридом 2,4,6-трихлорбензойной кислоты или активированной органическим хлоридом R3-CO-Cl, где R3 представляет собой алифатический или разветвленный C1-С30-алкил, гетероароматическую функциональную группу или ароматическую функциональную группу, в присутствии основания и катализатора в смеси воды и смешивающегося с водой апротонного растворителя.3. A method of obtaining a hyaluronic acid derivative of the general formula (I), characterized in that the hyaluronic acid is reacted with a C 6 -C 18 carboxylic acid activated with 2,4,6-trichlorobenzoic acid chloride or activated with an organic R 3 -CO- chloride Cl, where R 3 is an aliphatic or branched C 1 -C 30 -alkyl, heteroaromatic functional group or aromatic functional group, in the presence of a base and a catalyst in a mixture of water and a miscible aprotic solvent. 4. Способ получения по п. 3, отличающийся тем, что гиалуроновая кислота находится в свободной кислотной форме или в форме фармацевтически приемлемой соли и обладает молекулярной массой в предпочтительном диапазоне от 5×103 до 1,6×106 г/моль, более предпочтительно от 15×103 г/моль до 250×103 г/моль и наиболее предпочтительно от 15×103 до 50×103 г/моль.4. The production method according to p. 3, characterized in that the hyaluronic acid is in free acid form or in the form of a pharmaceutically acceptable salt and has a molecular weight in the preferred range of 5 × 10 3 to 1.6 × 10 6 g / mol, more preferably from 15 × 10 3 g / mol to 250 × 10 3 g / mol; and most preferably from 15 × 10 3 to 50 × 10 3 g / mol. 5. Способ получения по п. 3 или 4, отличающийся тем, что гиалуроновую кислоту растворяют в смеси воды и смешивающегося с водой апротонного растворителя, последнее представляет собой полярный органический растворитель, содержание воды находилось в диапазоне от 10 до 99% по объему, предпочтительно 50% по объему.5. The production method according to p. 3 or 4, characterized in that hyaluronic acid is dissolved in a mixture of water and a miscible aprotic solvent, the latter is a polar organic solvent, the water content was in the range from 10 to 99% by volume, preferably 50 % by volume. 6. Способ получения по п. 3 или 4, отличающийся тем, что смешивающийся с водой растворитель представляет собой диметилсульфоксид, тетрагидрофуран, ацетон, ацетонитрил или изопропанол.6. The production method according to p. 3 or 4, characterized in that the water miscible solvent is dimethyl sulfoxide, tetrahydrofuran, acetone, acetonitrile or isopropanol. 7. Способ получения по п. 3 или 4, отличающийся тем, что реакционная смесь содержит R'3N основание, где R' представляет собой неразветвленную или разветвленную CnHm-углеводородную цепь, где n представляет собой целое число в диапазоне от 1 до 4 и m представляет собой целое число в диапазоне от 3 до 9, например, триэтиламин, в количестве от 0,01 до 20 эквивалентов, предпочтительно 6 эквивалентов, по отношению к димеру гиалуроновой кислоты, и катализатор выбран из группы, включающей в себя замещенные пиридинины, такие как диметиламинопиридин, в количестве от 0,01 до 1 эквивалента, предпочтительно 0,05 эквивалента, по отношению к димеру гиалуроновой кислоты.7. The production method according to p. 3 or 4, characterized in that the reaction mixture contains an R ' 3 N base, where R' is a straight or branched C n H m hydrocarbon chain, where n is an integer in the range from 1 to 4 and m is an integer in the range from 3 to 9, for example triethylamine, in an amount of from 0.01 to 20 equivalents, preferably 6 equivalents, with respect to the hyaluronic acid dimer, and the catalyst is selected from the group consisting of substituted pyridinines, such as dimethylaminopyridine, in quantities from 0.01 to 1 equivalent, preferably 0.05 equivalent, relative to the hyaluronic acid dimer. 8. Способ получения по п. 3 или 4, отличающийся тем, что сначала активацию C6-C18-карбоновой кислоты проводят в полярном органическом растворителе в присутствии основания и 2,4,6-трихлорбензойной кислоты или ее производных, или в присутствии основания и органического хлорида, и впоследствии смесь, содержащую активированную С6-С18-карбоновую кислоту, добавляют к гиалуроновой кислоте, которая была растворена в смеси воды, органического растворителя, основания и катализатора, продуктом в результате реакции является производное общей формулы (I).8. The production method according to claim 3 or 4, characterized in that the activation of the C 6 -C 18 carboxylic acid is first carried out in a polar organic solvent in the presence of a base and 2,4,6-trichlorobenzoic acid or its derivatives, or in the presence of a base and organic chloride, and subsequently a mixture containing activated C 6 -C 18 carboxylic acid is added to hyaluronic acid, which was dissolved in a mixture of water, an organic solvent, a base and a catalyst, the product of the reaction is a derivative of the general formula (I) . 9. Способ получения по п. 3 или 4, отличающийся тем, что указанная С6-С18-карбоновая кислота выбрана из группы, содержащей капроновые, энантовые, каприловые, каприновые, пальмитиновые, стеариновые, олеиновые, линолевые и линоленовые кислоты.9. The production method according to claim 3 or 4, characterized in that said C 6 -C 18 carboxylic acid is selected from the group consisting of caproic, enanthic, caprylic, capric, palmitic, stearic, oleic, linoleic and linolenic acids. 10. Способ получения по п. 3 или 4, отличающийся тем, что количество активированной С6-С18-карбоновой кислоты находится в диапазоне от 0,01 до 5 эквивалентов, предпочтительно от 0,5 до 2 эквивалентов, по отношению к димеру гиалуроновой кислоты.10. The production method according to p. 3 or 4, characterized in that the amount of activated C 6 -C 18 carboxylic acid is in the range from 0.01 to 5 equivalents, preferably from 0.5 to 2 equivalents, with respect to the hyaluronic dimer acids. 11. Способ получения по п. 3 или 4, отличающийся тем, что активация С6-С18-карбоновой кислоты происходит в течение от 5 до 120 минут, предпочтительно в течение 30 минут, при температуре от 20 до 60°С, предпочтительно при температуре 25°С.11. The production method according to p. 3 or 4, characterized in that the activation of C 6 -C 18 carboxylic acid occurs within 5 to 120 minutes, preferably within 30 minutes, at a temperature of from 20 to 60 ° C, preferably at temperature 25 ° С. 12. Способ получения по п. 3 или 4, отличающийся тем, что взаимодействие гиалуроновой кислоты с активированной С6-С18-карбоновой кислотой происходит в течение от 1 до 24 часов, предпочтительно в течение от 2 до 3 часов, при температуре от 20 до 60°C, предпочтительно при температуре 25°С.12. The production method according to p. 3 or 4, characterized in that the interaction of hyaluronic acid with activated C 6 -C 18 carboxylic acid occurs within 1 to 24 hours, preferably within 2 to 3 hours, at a temperature of 20 up to 60 ° C, preferably at a temperature of 25 ° C. 13. Способ получения по п. 3 или 4, отличающийся тем, что С6-С18-ацилированное производное гиалуроновой кислоты впоследствии отделяют от реакционной смеси, промывают, сушат и лиофилизируют.13. The production method according to p. 3 or 4, characterized in that the C 6 -C 18 acylated derivative of hyaluronic acid is subsequently separated from the reaction mixture, washed, dried and lyophilized. 14. Способ получения по п. 13, отличающийся тем, что С6-С18-ацилированное производное гиалуроновой кислоты отделяют от реакционной смеси в процессе осаждения с применением NaCl и спирта.14. The production method according to p. 13, characterized in that the C 6 -C 18 acylated derivative of hyaluronic acid is separated from the reaction mixture during the precipitation using NaCl and alcohol. 15. Способ получения по п. 13, характеризующийся тем, что С6-С18-ацилированное производное гиалуроновой кислоты промывают спиртом, в частности изопропанолом или этанолом.15. The production method according to claim 13, characterized in that the C 6 -C 18 acylated derivative of the hyaluronic acid is washed with alcohol, in particular isopropanol or ethanol. 16. Наномицеллярная композиция на основе С6-С18-ацилированного производного гиалуроновой кислоты общей формулы (I), отличающаяся тем, что композиция содержит наномицеллы, которые включают в себя гидрофобное ядро, образованное С6-C18-ацильными группами, связанными с гиалуроновой кислотой, и гидрофильную оболочку, образованную гидрофильными функциональными группами гиалуроновой кислоты, одно или несколько биологически активных веществ были физически связаны в наномицелле.16. Nanomicellar composition based on a C 6 -C 18 acylated hyaluronic acid derivative of the general formula (I), characterized in that the composition contains nanomicelles, which include a hydrophobic core formed by C 6 -C 18 acyl groups associated with hyaluronic acid, and a hydrophilic shell formed by hydrophilic functional groups of hyaluronic acid, one or more biologically active substances were physically bound in a nanomicelle. 17. Наномицеллярная композиция по п. 16, отличающаяся тем, что она содержит от 0,3 до 50% по массе биологически активного вещества по отношению к массовому содержанию С6-С18-ацилированного производного гиалуроновой кислоты, биологически активное вещество было выбрано из группы, включающей в себя фармацевтически и косметически активные вещества, в частности, витамины, медикаменты, цитостатические средства, фитоэкстракты, фитокомплексы или фитоактивные вещества, минеральные или растительные масла, или их смесь.17. Nanomicellar composition according to claim 16, characterized in that it contains from 0.3 to 50% by weight of a biologically active substance with respect to the mass content of a C 6 -C 18 acylated derivative of hyaluronic acid, the biologically active substance was selected from the group including pharmaceutically and cosmetically active substances, in particular vitamins, medicines, cytostatic agents, phytoextracts, phytocomplexes or phytoactive substances, mineral or vegetable oils, or a mixture thereof. 18. Наномицеллярная композиция по п. 17, отличающаяся тем, что биологически активное вещество представляет собой токоферол, паклитаксел, фосфатидилхолин или кофермент Q10.18. Nanomicellar composition according to claim 17, characterized in that the biologically active substance is tocopherol, paclitaxel, phosphatidylcholine or coenzyme Q10. 19. Наномицеллярная композиция по п. 16, отличающаяся тем, что она содержит С6-C18-ацилированное производное гиалуроновой кислоты в концентрации, которая выше его критической концентрации агрегации.19. Nanomicellar composition according to claim 16, characterized in that it contains a C 6 -C 18 acylated derivative of hyaluronic acid at a concentration that is higher than its critical aggregation concentration. 20. Наномицеллярная композиция по п. 16, отличающаяся тем, что концентрация С6-С18-ацилированного производного гиалуроновой кислоты находится в диапазоне от 0,0001 мг·мл-1 до 30 мг·мл-1, предпочтительно от 1 до 20 мг·мл-1, если композиция представляет собой водный раствор.20. Nanomicellar composition according to claim 16, characterized in that the concentration of the C 6 -C 18 acylated derivative of hyaluronic acid is in the range from 0.0001 mg · ml -1 to 30 mg · ml -1 , preferably from 1 to 20 mg · Ml -1 , if the composition is an aqueous solution. 21. Наномицеллярная композиция по п. 16, отличающаяся тем, что биологически активное вещество представляет собой минеральное или растительное масло в количестве от 0,05 до 40% по массе, предпочтительно, от 1 до 20% по массе, по отношению к массовому содержанию С6-С18-ацилированного производного гиалуроновой кислоты.21. Nanomicellar composition according to claim 16, characterized in that the biologically active substance is a mineral or vegetable oil in an amount of from 0.05 to 40% by weight, preferably from 1 to 20% by weight, in relation to the mass content C 6 -C 18 acylated derivative of hyaluronic acid. 22. Наномицеллярная композиция по любому из пп. 16-21, отличающаяся тем, что она содержит биологически активное вещество, которое является жидким или нерастворимым в воде, указанное вещество содержит дополнительное биологически активное вещество, растворенное в нем.22. Nanomicellar composition according to any one of paragraphs. 16-21, characterized in that it contains a biologically active substance that is liquid or insoluble in water, the specified substance contains an additional biologically active substance dissolved in it. 23. Наномицеллярная композиция по п. 22, отличающаяся тем, что биологически активное вещество, которое является жидким или нерастворимым в воде, представляет собой минеральное или растительное масло, и дополнительное биологически активное вещество относится к фармацевтически или косметически активным веществам, в частности, витаминам, медикаментам, цитостатическим средствам, фитоэкстрактам, фитокомплексам или фитоактивным веществам, или к их смесям.23. Nanomicellar composition according to p. 22, characterized in that the biologically active substance, which is liquid or insoluble in water, is a mineral or vegetable oil, and the additional biologically active substance relates to pharmaceutically or cosmetically active substances, in particular vitamins, medicines, cytostatic agents, phytoextracts, phytocomplexes or phytoactive substances, or mixtures thereof. 24. Наномицеллярная композиция по любому из пп. 16-21 или п. 23, отличающаяся тем, что она находится в форме раствора, наноэмульсии, микроэмульсии, коацервата или геля.24. Nanomicellar composition according to any one of paragraphs. 16-21 or p. 23, characterized in that it is in the form of a solution, nanoemulsion, microemulsion, coacervate or gel. 25. Способ получения наномицеллярной композиции по любому из пп. 16-24, отличающийся тем, что С6-С18-ацилированное производное гиалуроновой кислоты общей формулы (I) растворяют в воде, биологически активное вещество растворяют в органическом растворителе, полученные растворы смешивают вместе, и впоследствии органический растворитель удаляют.25. A method of producing a nanomicellar composition according to any one of paragraphs. 16-24, characterized in that the C 6 -C 18 acylated hyaluronic acid derivative of the general formula (I) is dissolved in water, the biologically active substance is dissolved in an organic solvent, the resulting solutions are mixed together, and subsequently the organic solvent is removed. 26. Способ получения по п. 25, отличающийся тем, что органический растворитель удаляют при помощи выпаривания под вакуумом, впоследствии водную фазу сушат и регидратируют, и полученные наномицеллярные структуры фильтруют и в конечном итоге лиофилизируют.26. The production method according to p. 25, characterized in that the organic solvent is removed by evaporation under vacuum, the aqueous phase is subsequently dried and rehydrated, and the resulting nanomicellar structures are filtered and ultimately lyophilized. 27. Способ получения по п. 24, отличающийся тем, что органический растворитель удаляют при помощи диализа, впоследствии полученные наномицеллярные структуры фильтруют и в конечном итоге лиофилизируют.27. The production method according to p. 24, characterized in that the organic solvent is removed by dialysis, subsequently the resulting nanomicellar structures are filtered and finally lyophilized. 28. Способ получения по любому из пп. 25-27, отличающийся тем, что органический растворитель представляет собой летучий хлорированный растворитель, такой как трихлорметан, или спирт, такой как этанол или изопропанол.28. The production method according to any one of paragraphs. 25-27, wherein the organic solvent is a volatile chlorinated solvent, such as trichloromethane, or an alcohol, such as ethanol or isopropanol. 29. Способ получения наномицеллярной композиции по п. 16, отличающийся тем, что С6-С18-ацилированное производное гиалуроновой кислоты общей формулы (I) растворяют в воде, и впоследствии смешивают вместе с биологически активным веществом, которое является жидким или нерастворимым в воде, после чего полученную смесь гомогенизируют при помощи обработки ультразвуком с образованием микроэмульсии или наноэмульсии.29. A method of producing a nanomicellar composition according to claim 16, characterized in that the C 6 -C 18 acylated hyaluronic acid derivative of the general formula (I) is dissolved in water and subsequently mixed with a biologically active substance that is liquid or insoluble in water after which the resulting mixture is homogenized by sonication to form a microemulsion or nanoemulsion. 30. Способ получения наномицеллярной композиции по п. 22 или 23, отличающийся тем, что С6-С18-ацилированное производное гиалуроновой кислоты общей формулы (I) растворяют в воде, и впоследствии смешивают вместе с биологически активным веществом, которое является жидким или нерастворимым в воде, и в котором растворено дополнительное биологически активное вещество, после чего полученную смесь гомогенизируют при помощи обработки ультразвуком с образованием микроэмульсии или наноэмульсии.30. A method of producing a nanomicellar composition according to claim 22 or 23, characterized in that the C 6 -C 18 acylated hyaluronic acid derivative of the general formula (I) is dissolved in water and subsequently mixed with a biologically active substance that is liquid or insoluble in water, and in which an additional biologically active substance is dissolved, after which the resulting mixture is homogenized by sonication to form a microemulsion or nanoemulsion. 31. Применение наномицеллярной композиции по любому из пп. 16-24 при фармацевтических или косметических применениях, предпочтительно при местных применениях.31. The use of the nanomicellar composition according to any one of paragraphs. 16-24 for pharmaceutical or cosmetic applications, preferably for topical applications. 32. Способ получения стабилизированной наномицеллярной композиции, отличающийся тем, что получают С6-С18-ацилированный гиалуронан общей формулы (II):32. A method for producing a stabilized nanomicellar composition, characterized in that C 6 -C 18 acylated hyaluronan of the general formula (II) is prepared:
Figure 00000002
Figure 00000002
 где R представляет собой H+ или Na+, один или несколько R1 членов представляют собой неразветвленную С6-С18-цепь по меньшей мере в одной повторяющейся единице, при этом неразветвленная цепь может содержать ненасыщенные связи, и 3-(2-тиенил)акриловую кислоту или 3-(2-фурил)акриловую кислоту или производные указанных кислот в другой по меньшей мере одной повторяющейся единице, при этом наномицеллярную композицию получают из С6-С18-ацилированного гиалуронана общей формулы (II), такую композицию затем стабилизируют при помощи реакции сшивания.where R represents H + or Na + , one or more R 1 members are an unbranched C 6 -C 18 chain in at least one repeating unit, wherein the unbranched chain may contain unsaturated bonds, and 3- (2-thienyl ) acrylic acid or 3- (2-furyl) acrylic acid or derivatives of these acids in another at least one repeating unit, wherein the nanomicellar composition is obtained from a C 6 -C 18 acylated hyaluronan of the general formula (II), such a composition is then stabilized using a crosslinking reaction. 33. Способ получения по п. 32, отличающийся тем, что сначала осуществляют взаимодействие гиалуроновой кислоты с 3-(2-тиенил)акриловой кислотой или 3-(2-фурил)акриловой кислотой или с производным любой кислоты в присутствии основания и катализатора в смеси воды и смешивающегося с водой апротонного растворителя, указанные кислоты были активированы хлоридом 2,4,6-трихлорбензойной кислоты или активированы органическим хлоридом R3-CO-Cl, где R3 представляет собой алифатический или разветвленный C1-С30-алкил, возможно содержащий гетероароматическую или ароматическую функциональную группу, с образованием акрилированного гиалуронана формулы (III):33. The production method according to p. 32, characterized in that the hyaluronic acid is first reacted with 3- (2-thienyl) acrylic acid or 3- (2-furyl) acrylic acid or with a derivative of any acid in the presence of a base and a catalyst in a mixture water and a water-miscible aprotic solvent, these acids were activated with 2,4,6-trichlorobenzoic acid chloride or activated with organic chloride R 3 -CO-Cl, where R 3 is an aliphatic or branched C 1 -C 30 alkyl, possibly containing heteroaromatic and whether an aromatic functional group, with the formation of acrylated hyaluronan of the formula (III):
Figure 00000003
Figure 00000003
Figure 00000004
Figure 00000004
 после этого осуществляют взаимодействие акрилированного гиалуронана формулы (III) с С6-С18-карбоновой кислотой, активированной хлоридом 2,4,6-трихлорбензойной кислотой или активированной органическим хлоридом R3-CO-Cl, где R3 представляет собой алифатический или разветвленный C1-С30-алкил, по мере необходимости содержащий гетероароматическую или ароматическую функциональную группу, в присутствии основания и катализатора в смеси воды и смешивающегося с водой апротонного растворителя с образованием С6-С18-ацилированного гиалуронана формулы (II), впоследствии наномицеллярную композицию получают из указанного гиалуронана формулы (II) с применением способа по любому из пп. 25-30, при этом композицию затем подвергают реакции сшивания при помощи реакций радикального типа.thereafter, the acrylated hyaluronan of formula (III) is reacted with a C 6 -C 18 carboxylic acid activated with 2,4,6-trichlorobenzoic acid chloride or activated with organic chloride R 3 -CO-Cl, where R 3 is an aliphatic or branched C C 1 -C 30 -alkyl, where appropriate containing aromatic or heteroaromatic functional group in the presence of a base and a catalyst in a mixture of water and an aprotic solvent miscible with water to form C 6 -C 18 -acylated forms of hyaluronan ly (II), subsequently nanomitsellyarnuyu composition prepared from said hyaluronan formula (II) using the method according to any one of claims. 25-30, wherein the composition is then subjected to a crosslinking reaction using radical type reactions. 34. Способ получения по любому из пп. 32 и 33, отличающийся тем, что реакцию радикального типа катализируют при помощи сшивающего агента.34. The production method according to any one of paragraphs. 32 and 33, characterized in that the radical type reaction is catalyzed using a crosslinking agent. 35. Способ получения по п. 34, отличающийся тем, что сшивающий агент представляет собой пероксодисульфат аммония.35. The production method according to p. 34, wherein the crosslinking agent is ammonium peroxodisulfate.
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